Wicker Park watering holes
What compelled a James Beard Award–winning chef and the owners of one of the city’s most exclusive cocktail lounge to open a divey bar that slings Tecates and whiskey shots for $3 apiece? A stroke of absolute genius. Brutal crowds harsh the country-music mellow on weekends, but neighborhood hipsters put up with it, dropping by the takeout window to grab a couple of tacos or planting themselves at the bar for a few beers or quality cocktails. 1531 N Damen Ave (773-235-4039). Sun–Fri 11:30am–2am; Sat 11:30am–3am. Average beer: $4.
bin wine café
You could easily make a meal of wine and cheese at this bustling Wicker Park wine bar, but you may have a hard time resisting going further (especially in summer, when the sidewalk patio invites lingering over seasonal small plates). Try starting with a wine flight assembled by sommelier Jan Henricksen, and if you find something you like, bottles are sold for the road. 1559 N Milwaukee Ave (773-486-2233). Mon–Thu 4–10pm; Fri 4–midnight; Sat 4pm–midnight; Sun 10am–3pm. Average glass of wine: $7.
This beer-focused tavern didn’t intend to be such a food destination, but the eats here get a lot of attention. Tempting small plates, such as harissa-spiced chicken wings and smoked trout riette, are tough to choose from, so don’t; spend the evening grazing while sampling the vast beer list. Don’t know good suds from duds? The staff members are pretty well-versed, and even when they’re slammed on weekend nights, they tend to field questions or offer up suggestions. 1749 N Damen Ave (773-486-2473). Sun–Fri 5pm–1:30am; Sat 5pm–2:30am. Average small plate: $10.
Handlebar Bar & Grill
The multiple bike racks out back are packed with every kind of two-wheeler imaginable, no matter the time of year at this biker bar (and by biker, we mean bicycler). Eco-minded folks chat over tasty vegan fare (the barbecue seitan is great), check out each other’s rides and sample from the ample list of diverse drafts. 2311 W North Ave (773-384-9546). Daily 10am–1am. Average beer: $5.
The Violet Hour
This hip cocktail lounge is exactly what you’d expect from a bar named after a line of T.S. Eliot poetry: pristine (the carefully constructed cocktails are excellent), pretentious (you won’t find a sign on the door—just look for the long lines) and, ultimately, completely and inarguably gorgeous. 1520 N Damen Ave (773-252-1500). Sun–Fri 6pm–2am; Sat 6pm–3am. Average cocktail: $12.